title: Synthesis and tautomerization of benzo[cd]azulen-3-ones.
abstract: This report describes a type of tautomerization reaction that proceeds via isomerization of π-bonds across the azulene moieties of tricyclic benzo[cd]azulen-3-ones. The reaction mechanism shows similarities to an elimination reaction that was recently developed in our group. Furthermore, the facile four-step syntheses of the benzo[cd]azulen-3-ones, the starting materials for the tautomerization reactions, and computational analyses of the tautomerization reaction are included.
authors.affiliation: Faculty of Pharmacy, Division of Pharmaceutical Chemistry, P.O. Box 56 (Viikinkaari 5 E), FI-00014, University of Helsinki, Finland.
authors.forename: Ingo B
authors.initials: IB
authors.lastname: Aumüller
authors.forename: Jari
authors.initials: J
authors.lastname: Yli-Kauhaluoma
mesh_terms: D052176:Azulenes / Q000138:chemical synthesis*; D001554:Benzene / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D052176:Azulenes; D001554:Benzene